Oxidatively induced glycosylation starting from hydroquinone glycosides

作者: Hans Günter Thomas , Jean-Luc Mieusset

DOI: 10.1016/J.TET.2008.03.056

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摘要: Abstract As a new class of glycosyl donors, hydroquinone glycosides can be used for glycosylation reactions. Their activation performed either electrochemically or under homogeneous chemical conditions. Conventionally, several glucosides were produced with yields greater than 77% using DDQ in CH 2 Cl as oxidizing agent. For electrolyses, trimethylhydroquinone are preferably because their low oxidation potentials allow the utilization an undivided cell. The synthesis donors was achieved high efficiency by direct coupling phenols peracetylated monosaccharides employing boron trifluoride etherate catalyst. derivatives also applied to generation other stabilized cations.

参考文章(52)
Géza Zemplén, Zoltán Csürös, Stefan Angyal, Über benzylierte Derivate des Lävoglucosans und der Glucose Berichte der deutschen chemischen Gesellschaft (A and B Series). ,vol. 70, pp. 1848- 1856 ,(1937) , 10.1002/CBER.19370700903
Ryoji Noyori, Isao Kurimoto, Electrochemical glycosylation method Journal of Organic Chemistry. ,vol. 51, pp. 4320- 4322 ,(1986) , 10.1021/JO00372A050
Geert-Jan Boons, Strategies in Oligosaccharide Synthesis Tetrahedron. ,vol. 52, pp. 1095- 1121 ,(1996) , 10.1016/0040-4020(95)00897-7
David Brevet, Yves Mugnier, Soth Samreth, Philippe Dellis, New efficient electrochemical synthesis of 1,5-dithioxylopyranosides in the presence of a sacrificial anode Carbohydrate Research. ,vol. 338, pp. 1543- 1552 ,(2003) , 10.1016/S0008-6215(03)00205-2
Likun Han, Wei Li, Sanae Narimatsu, Lijuan Liu, Hongwei Fu, Hiromichi Okuda, Kazuo Koike, Inhibitory effects of compounds isolated from fruit of Juglans mandshurica on pancreatic lipase Journal of Natural Medicines. ,vol. 61, pp. 184- 186 ,(2007) , 10.1007/S11418-006-0109-4
Zühal Güvenalp, Cavit Kazaz, Yusuf Kaya, L. Ömür Demirezer, Phytochemical investigation on Galium humifusum growing in Turkey Biochemical Systematics and Ecology. ,vol. 34, pp. 894- 896 ,(2006) , 10.1016/J.BSE.2006.07.005
Richard W. Johnson, M.D. Bednarski, B.F. O'Leary, E.R. Grover, Electrochemical transacylations: A mild synthesis of esters Tetrahedron Letters. ,vol. 22, pp. 3715- 3718 ,(1981) , 10.1016/S0040-4039(01)82001-3
Wilhelm Treibs, Inge Franke, Über die Synthese und Spaltung der β‐d‐Glucoside der Menthol‐Reihe European Journal of Organic Chemistry. ,vol. 570, pp. 76- 87 ,(1950) , 10.1002/JLAC.19505700108